50%酢酸中での過酢酸と塩化ベンゼンジアゾニウム類の反応 : o-クロロフェノール生成の機構

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In the decomposition of benzenediazonium chloride (BDC) in the presence of peracetic acid, o-chlorophenol (OCP) was obtained. When the molar ratio of peracetic acid against BDC was less than unity, only OCP was obtained. The sum of the yields of parachlorinated products such as p-chlorophenol, 2, 4-dichlorophenol (2, 4-DCP) and 2, 4, 6-trichlorophenol (TCP), incresed with the molar ratio. p-Toluenediazonium chloride (TDC) also showed the same tendency. It should be noted that in no case was 2-chloro-p-cresol (OCPC) formed without peracetic acid, but p-cresol (PC), p-chlorotoluene (PCT) and p-tolyl acetate (PTA) were formed. No toluene or p, p-bitolyl could be detected. The rate constant for the consumption reaction of peracetic acid in the titled decomposition reaction of BDC was equal to that in the reaction with phenol instead of BDC, and smaller than that of the decomposition of BDC. This should be the rate constant for the formation of chlorinating species, considered to be acetyl hypochlorite, judging from the o/p ratio of chlorophenol formed. In the reaction of TDC, the rate constant for the consumption of peracetic acid was greater than the decomposition rate constant of TDC equal to that for the formation of any product. From these findings, a probable mechanism involving an attack of acetyl hypochlorite formed by the oxidation of chloride anion with peracetic acid on phenols produced by the ionic decomposition of benzenediazonium chlorides is postulated and discussed.
社団法人日本油化学会の論文

50%酢酸中での過酢酸と塩化ベンゼンジアゾニウム類の反応 : <I>o</I>-クロロフェノール生成の機構

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